Modern vehicle systems may have entertainment features that are accessible to users for the duration of the trip. For example, users who are passengers can view media content on screens built into the vehicle in addition to viewing media content on personal user devices. As cars become more and more automated, the demand for in-trip entertainment is increasing. Fully autonomous (self-driving) vehicles do not require a driver and thus may provide entertainment options for all passengers. Additionally, autonomous vehicles may include screens where previously unfeasible, e.g., on the windshield or a side window. Furthermore, modern vehicle systems often have access to the trip itinerary data. Modern vehicle systems may, at best, select media content to fill up the trip duration. However, vehicle systems lack any way to intelligently select media content for presentation in order to take advantage of the trip itinerary data to maximally interest the viewer and incentivize the user to continue watching the media content after the present trip is over.